Title: Book the Best Winter Park, FL ALL INCLUSIVE Resorts and Hotels | Expedia.ca [Hotels in Winter Park](https://expedia.ca/Winter-Park-Hotels.d7902.Travel-Guide-Hotels)[Vacation Rentals in Winter Park](https://expedia.ca/Winter-Park-Vacation-Rentals.d7902.Travel-Guide-VacationRentals)[Flights to Winter Park](https://expedia.ca/Cheap-Flights-To-Winter-Park.d7902.Travel-Guide-Flights)[Winter Park Car Rentals](https://expedia.ca/Car-Rentals-In-Winter-Park.d7902.Car-Rental-Guide)[Winter Park Vacation Packages](https://expedia.ca/Winter-Park.d7902.Destination-Travel-Guides) ![Kraft Azalea Gardens showing a fountain, a park and a pond](https://images.trvl-media.com/place/553248621532654339/aef9d03a-cd86-4dcc-8e9d-049aef598da5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find All Inclusive Resorts and Hotels in Winter Park, FL - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Winter Park All Inclusive Resorts and Hotels Tonight [Dec 1 - Dec 2](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-12-01&endDate=2025-12-02&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 2 - Dec 3](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-12-02&endDate=2025-12-03&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-12-05&endDate=2025-12-07&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-12-12&endDate=2025-12-14&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winter Park All Inclusive Resorts and Hotels ![Reception](https://images.trvl-media.com/lodging/46000000/45490000/45488100/45488005/25e0761c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/46000000/45490000/45488100/45488005/38f26455.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/46000000/45490000/45488100/45488005/368acdbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/46000000/45490000/45488100/45488005/fbeb2b17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Winter Park Winter Park 9.2/10 Wonderful (622) "The dining options close by are increasing and the area is becoming more attractive" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Antonio CA $278 CA $316 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Orlando-Hotels-Hilton-Garden-Inn-Winter-Park.h45488005.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/19800/19791/51fdc461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily cooked-to-order breakfast for a fee](https://images.trvl-media.com/lodging/1000000/20000/19800/19791/3dec6392.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/20000/19800/19791/fcdf7880.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 10:00 AM to 5:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/19800/19791/2186e4f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Alfond Inn Winter Park 9.6/10 Exceptional (1016) "Beautiful hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paige [](https://www.expedia.ca/Orlando-Hotels-The-Alfond-Inn.h19791.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1790000/1784900/1784873/21834885.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1790000/1784900/1784873/52e0ae75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front Side Balcony Suite, 1 King](https://images.trvl-media.com/lodging/2000000/1790000/1784900/1784873/96b386a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/2000000/1790000/1784900/1784873/450d6e5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Park Plaza Hotel Park Avenue District 8.6/10 Excellent (1007) "Perfect location! Older hotel so don’t go in expecting the Hilton but the balcony and location more than make up for it. Will stay here again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle CA $222 CA $250 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Orlando-Hotels-Park-Plaza-Hotel.h1784873.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-15&endDate=2025-12-16®ionId=7902&adults=2&mealPlan=ALL_INCLUSIVE&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_7902) ## Top Winter Park Hotel Reviews ![Hyatt Regency Orlando](https://images.trvl-media.com/lodging/1000000/10000/9600/9574/1bb0a2ac_y.jpg) ### Hyatt Regency Orlando 10/10 Excellent "the room was very clean, safe walkable area. Descend 21 is quite overpriced but expected for hotel restaurant. " [](https://expedia.ca/Orlando-Hotels-Hyatt-Regency-Orlando.h9574.Hotel-Information) ## Frequently asked questions ### How much does an all-inclusive hotel in Winter Park cost? > Enjoy staying in an all-inclusive hotel in Winter Park, with hotels from CA $250 offering incredible amenities. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays. ### What area of Winter Park is best for all-inclusive hotels? > The Winter Park area in Florida is a delightful choice for travellers seeking all-inclusive hotels, blending natural beauty with cultural richness. This charming town, known for its picturesque lakes and lush gardens, is just a stone's throw from Orlando, making it a convenient retreat. Visitors can enjoy the scenic beauty of the Central Park and the enchanting landscapes of the Harry P. Leu Gardens, while also having access to upscale dining and shopping options along Park Avenue. > > > > For couples craving a romantic escape, the boutique hotels in the heart of Winter Park offer a superb blend of luxury and intimacy. Imagine waking up to serene lake views and indulging in gourmet breakfasts before exploring the local art scene, which includes the renowned Charles Hosmer Morse Museum of American Art, home to an impressive collection of Tiffany glass. > > > > Families, on the other hand, will appreciate the family-friendly all-inclusive resorts that cater to both relaxation and adventure. Spacious accommodations and kid-friendly activities make it easy for parents to unwind while the little ones are entertained. Plus, the nearby attractions in Orlando, like theme parks and interactive experiences, ensure that there are countless opportunities for fun-filled days together. ### What is the best time to stay at an all-inclusive hotel in Winter Park? > The most popular time to stay at an all-inclusive hotel in Winter Park, Florida, is during the winter months, particularly from December to March. During this period, temperatures typically range from 15°C to 25°C, making it ideal for enjoying outdoor activities and the natural beauty of the area. This season sees an influx of tourists, drawn by the mild weather and the opportunity to escape colder climates. > > > > With the pleasant temperatures, guests can take advantage of the many outdoor activities available, such as hiking in the nearby parks or exploring the scenic lakes. The winter months also coincide with several local events, including the Winter Park Sidewalk Art Festival in March, which attracts art lovers and families alike. However, it's worth noting that this is peak season, so popular attractions can be busy, and advance bookings are recommended for the best experiences. > > > > If you're looking for a great alternative, consider visiting in November. The weather remains mild, with temperatures around 20°C, and you'll enjoy a more relaxed atmosphere with fewer tourists. This shoulder month offers excellent value for accommodation and activities, allowing you to experience the charm of Winter Park without the winter crowds. ### How can I save on an all-inclusive hotel in Winter Park with Expedia? > There are plenty of ways to save on an all-inclusive hotel in Winter Park. Join [One Key™](https://www.expedia.ca/welcome-one-key)—Expedia's free travel rewards program—to access discounted Member Prices and member-only perks. Typically, booking in advance will help you save on your all-inclusive hotel. If you're feeling spontaneous, be sure to check for last-minute deals. ### Is it cheaper to book an all-inclusive hotel and flight package in Winter Park? > Booking an all-inclusive hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect all-inclusive travel package. ### What all-inclusive amenities should we expect at hotels in Winter Park? > All-inclusive hotels are perfect for travellers who want a relaxing, top-value vacation. Most packages include your room, all meals, snacks, unlimited drinks including alcohol and non-alcoholic drinks. Entertainment, kids' clubs, access to pools and fitness facilities are often included in the all-inclusive package as well. Some even cover airport transfers, while extras like spa treatments or premium alcohol may cost more. Knowing most of your expenses are already covered makes for a truly relaxing getaway. For more information, refer to the property details on Expedia. ### Can I cancel my all-inclusive hotel reservation on Expedia? > Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. 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